Personal blog of Yzmir Ramirez

The pandemic has been a time for a lot of reflection on both a personal and business level. Tech companies in particular are assessing whether they will ever again return to a full time, in-office approach. Some are considering a hybrid approach and some may not go back to a building at all. Amidst all this, Dropbox has decided to reimagine the office with a new concept they are introducing this week called Dropbox Studios.

Dropbox CEO and co-founder Drew Houston sees the pandemic as a forcing event, one that pushes companies to rethink work through a distributed lens. He doesn’t think that many businesses will simply go back to the old way of working. As a result, he wanted his company to rethink the office design with one that did away with cube farms with workers spread across a landscape of cubicles. Instead, he wants to create a new approach that takes into account that people don’t necessarily need a permanent space in the building.

“We’re soft launching or opening our Dropbox Studios [this] week in the U.S., including the one in San Francisco. And we took the opportunity as part of our focus to reimagine the office into a collaborative space that we call a studio,” Houston told me.

Houston says that the company really wanted to think about how to incorporate the best of working at home with the best of working at the office collaborating with colleagues. “We focused on having really great curated in-person experiences, some of which we coordinate at the company level and then some of which you can go into our studios, which have been refitted to support more collaboration,” he said.

Dropbox Studio coffee shop Image Credit: Dropbox

To that end, they have created a lot of soft spaces with a coffee shop to create a casual feel, conference rooms for teams to have what Houston called “on-site off-sites” and classrooms for organized group learning. The idea is to create purpose-built spaces for what would work best in an office environment and what people have been missing from in-person interactions since they were forced to work at home by the pandemic, while letting people accomplish more individual work at home.

The company is planning on dedicated studios in major cities like San Francisco, Seattle, Tokyo and Tel Aviv with smaller on demand spaces operated by partners like WeWork in other locations.

Dropbox Studio classroom space Image Credits: Dropbox

As Houston said when he appeared at TechCrunch Disrupt last year, his company sees this as an opportunity to be on the forefront of distributed work and act as an example and a guide to help other companies as they undertake similar journeys.

“When you think more broadly about the effects of the shift to distributed work, it will be felt well beyond when we go back to the office. So we’ve gone through a one-way door. This is maybe one of the biggest changes to knowledge work since that term was invented in 1959,” Houston said last year.

He recognizes that they have to evaluate how this is going to work and iterate on the design as needed, just as the company iterates on its products and they will be evaluating the new spaces and the impact on collaborative work and making adjustments when needed. To help others, Dropbox is releasing an open source project plan called the Virtual First Toolkit.

The company is going all in with this approach and will be subletting much of its existing office space as it moves to this new way of working and its space requirements change dramatically. It’s a bold step, but one that Houston believes his company is uniquely positioned to undertake, and he wants Dropbox to be an example to others on how to reinvent the way we work.

Dropbox announced today that it plans to acquire DocSend for $165 million. The company helps customers share and track documents by sending a secure link instead of an attachment.

“We’re announcing that we’re acquiring DocSend to help us deliver an even broader set of tools for remote work, and DocSend helps customers securely manage and share their business-critical documents, backed by powerful engagement analytics,” Dropbox CEO Drew Houston told me.

When combined with the electronic signature capability of HelloSign, which Dropbox acquired in 2019, the acquisition gives the company an end-to-end document-sharing workflow it had been missing. “Dropbox, DocSend and HelloSign will be able to offer a full suite of self-serve products to help our millions of customers manage the entire critical document workflows and give more control over all aspects of that,” Houston explained.

Houston and DocSend co-founder and CEO Russ Heddleston have known each for other years, and have an established relationship. In fact, Heddleston worked for Dropbox as a summer in intern in 2010. He even ran the idea for the company by Houston prior to launching in 2013, who gave it his seal of approval, and the two companies have been partners for some time.

“We’ve just been following the thread of external sending, which has just kind of evolved and opened up into all these different workflows. And it’s just really interesting that by just being laser-focused on that we’ve been able to create a really differentiated product that users love a ton,” Heddleston said.

Those workflows include creative, sales, client services or startups using DocSend to deliver proposals or pitch decks and track engagement. In fact, among the earliest use cases for the company was helping startups track engagement with their pitch decks at VC firms.

The company raised a modest amount of the money along the way, just $15.3 million, according to Crunchbase, but Heddleston says that he wanted to build a company that was self-sufficient and raising more VC dollars was never a priority or necessity. “We had [VCs] chase us to give us more money all the time, and what we would tell our employees is that we don’t keep count based on money raised or headcount. It’s just about building a great company,” he said.

That builder’s attitude was one of the things that attracted Houston to the company. “We’re big believers in the model of product growth and capital efficiency, and building really intuitive products that are viral, and that’s a lot of what what attracted us to DocSend,” Houston said. While DocSend has 17,000 customers, Houston says the acquisition gives the company the opportunity to get in front of a much larger customer base as part of Dropbox.

It’s worth noting that Box offers a similar secure document-sharing capability enabling users to share a link instead of using an attachment. It recently bought e-signature startup SignRequest for $55 million with an eye toward building more complex document workflows similar to what Dropbox now has with HelloSign and DocSend. PandaDoc is another competitor in this space.

Both Dropbox and DocSend participated in the TechCrunch Disrupt Battlefield, with Houston debuting Dropbox in 2008 at the TechCrunch 50, the original name of the event. Meanwhile, DocSend participated in 2014 at TechCrunch Disrupt in New York City.

DocSend’s approximately 50 employees will be joining Dropbox when the deal closes, which should happen soon, subject to standard regulatory oversight.

In a September interview at TechCrunch Disrupt, Dropbox co-founder and CEO Drew Houston talked about how the pandemic had forced the company to rethink what work means, and how his company is shifting with the new requirements of a work-from-home world. Today, the company announced broad changes to Dropbox Spaces, the product introduced last year, to make it a collaboration and project management tool designed with these new requirements in mind.

Dropbox president Timothy Young says that the company has always been about making it easy to access files wherever you happen to be and whatever device you happen to be on, whether that was in a consumer or business context. As the company has built out its business products over the last several years, that involved sharing content internally or externally. Today’s announcement is about helping teams plan and execute around the content you create with a strong project focus.

“Now what we’re basically trying to do is really help distributed teams stay organized, collaborate together and keep moving along, but also do so in a really secure way and support IT, administrators and companies with some features around that as well, while staying true to Dropbox principles,” Young said.

This involves updating Spaces to be a full-fledged project management tool designed with a distributed workforce in mind. Spaces connects to other tools like your calendar, people directory, project management software — and of course files. You can create a project, add people and files, then set up a timeline and assign and track tasks, In addition, you can access meetings directly from Spaces and communicate with team members, who can be inside or outside the company.

Houston suggested a product like this could be coming in his September interview when he said:

“Back in March we started thinking about this, and how [the rapid shift to distributed work] just kind of happened. It wasn’t really designed. What if you did design it? How would you design this experience to be really great? And so starting in March we reoriented our whole product road map around distributed work,” he said.

Along these same lines, Young says the company itself plans to continue to be a remote first company even after the pandemic ends, and will continue to build tools to make it easier to collaborate and share information with that personal experience in mind.

Today’s announcement is a step in that direction. Dropbox Spaces has been in private beta and should be available at the beginning of next year.

Dropbox CEO and co-founder Drew Houston, appearing at TechCrunch Disrupt today, said that COVID has accelerated a shift to distributed work that we have been talking about for some time, and these new ways of working will not simply go away when the pandemic is over.

“When you think more broadly about the effects of the shift to distributed work, it will be felt well beyond when we go back to the office. So we’ve gone through a one-way door. This is maybe one of the biggest changes to knowledge work since that term was invented in 1959,” Houston told TechCrunch Editor-In-Chief Matthew Panzarino.

That change has prompted Dropbox to completely rethink the product set over the last six months, as the company has watched the way people work change in such a dramatic way. He said even though Dropbox is a cloud service, no SaaS tool in his view was purpose-built for this new way of working and we have to reevaluate what work means in this new context.

“Back in March we started thinking about this, and how [the rapid shift to distributed work] just kind of happened. It wasn’t really designed. What if you did design it? How would you design this experience to be really great? And so starting in March we reoriented our whole product road map around distributed work,” he said.

He also broadly hinted that the fruits of that redesign are coming down the pike. “We’ll have a lot more to share about our upcoming launches in the future,” he said.

Houston said that his company has adjusted well to working from home, but when they had to shut down the office, he was in the same boat as every other CEO when it came to running his company during a pandemic. Nobody had a blueprint on what to do.

“When it first happened, I mean there’s no playbook for running a company during a global pandemic so you have to start with making sure you’re taking care of your customers, taking care of your employees, I mean there’s so many people whose lives have been turned upside down in so many ways,” he said.

But as he checked in on the customers, he saw them asking for new workflows and ways of working, and he recognized there could be an opportunity to design tools to meet these needs.

“I mean this transition was about as abrupt and dramatic and unplanned as you can possibly imagine, and being able to kind of shape it and be intentional is a huge opportunity,” Houston said.

Houston debuted Dropbox in 2008 at the precursor to TechCrunch Disrupt, then called the TechCrunch 50. He mentioned that the Wi-Fi went out during his demo, proving the hazards of live demos, but offered words of encouragement to this week’s TechCrunch Disrupt Battlefield participants.

Although his is a public company on a $1.8 billion run rate, he went through all the stages of a startup, getting funding and eventually going public, and even today as a mature public company, Dropbox is still evolving and changing as it adapts to changing requirements in the marketplace.

According to Dropbox CEO Drew Houston, 80% of the product’s users rely on it, at least partially, for work.

It makes sense, then, that the company is refocusing to try and cement its spot in the workplace; to shed its image as “just” a file storage company (in a time when just about every big company has its own cloud storage offering) and evolve into something more immutably core to daily operations.

Earlier this week, Dropbox announced that the “new Dropbox” would be rolling out to all users. It takes the simple, shared folders that Dropbox is known for and turns them into what the company calls “Spaces” — little mini collaboration hubs for your team, complete with comment streams, AI for highlighting files you might need mid-meeting, and integrations into things like Slack, Trello and G Suite. With an overhauled interface that brings much of Dropbox’s functionality out of the OS and into its own dedicated app, it’s by far the biggest user-facing change the product has seen since launching 12 years ago.

Shortly after the announcement, I sat down with Dropbox VP of Product Adam Nash and CTO Quentin Clark . We chatted about why the company is changing things up, why they’re building this on top of the existing Dropbox product, and the things they know they just can’t change.

You can find these interviews below, edited for brevity and clarity.

Greg Kumparak: Can you explain the new focus a bit?

Adam Nash: Sure! I think you know this already, but I run products and growth, so I’m gonna have a bit of a product bias to this whole thing. But Dropbox… one of its differentiating characteristics is really that when we built this utility, this “magic folder”, it kind of went everywhere.

Dropbox is a critically important tool for more than 500 million people, which is why we’re so excited to have founder and CEO Drew Houston on the Disrupt stage in September.

Dropbox launched back in 2007 and Houston has spent the last decade growing Dropbox to the behemoth it is today.

During that time, Houston has made some tough decisions.

A few years ago, Houston decided to move the Dropbox infrastructure off of AWS. In 2014, Houston chose to raise $500 million in debt financing to keep up pace with Box, which was considering an IPO at the time. And in March 2017, Dropbox took another $600 million in debt financing from JP Morgan.

Houston also reportedly turned down a nine-figure acquisition offer from Apple.

All the while, Houston led Dropbox to be cash-flow positive and grew the company to see a $1 billion revenue run rate as of last year.

And, of course, we can’t forget the decision to go public earlier this year.

Interestingly, Houston first told his story to a TechCrunch audience at TC50 in 2008 as part of the Startup Battlefield. In fact, you can check out the original pitch from TC50 right here.

At Disrupt SF in September, we’re excited to sit down with Houston to discuss his journey thus far, the decision to go public and the future of Dropbox.

The show runs from September 5 to September 7, and for the next week, our super early-bird tickets are still available.

Dropbox went public this morning to great fanfare, with the stock shooting up more than 40% in the initial moments of trading as the enterprise-slash-consumer company looked to convince investors that it could be a viable publicly-traded company.

And for one that Steve Jobs famously called a feature, and not a company, it certainly was an uphill battle to convince the world that it was worth even the $10 billion its last private financing round set. It’s now worth more than that, but that follows a long series of events, including an increased focus on enterprise customers and finding ways to make its business more efficient — like installing their own infrastructure. Dropbox CEO Drew Houston acknowledged a lot of this, as well as the fact that it’s going to continue to face the challenge of ensuring that its users and enterprises will trust Dropbox with some of their most sensitive files.

We spoke with Houston on the day of the IPO to talk a little bit about what it took to get here during the road show and even prior. Here’s a lightly-edited transcript of the conversation:

TC: In light of the problems that Facebook has had surrounding user data and user trust, how has that changed how you think about security and privacy as a priority?

DH: Our business is built on our customers’ trust. Whether we’re private or public, that’s super important to us. I think, to our customers, whether we’re private or public doesn’t change their view. I wouldn’t say that our philosophy changes as we get to bigger and bigger scale. As you can imagine we make big investments here. We have an awesome security team, our first cultural principle is be worthy of trust. This is existential for us.

TC: How’s the vibe now that longtime employees are going to have an opportunity to get rewarded for their work now that you’re a public company?

DH: I think everyone’s just really excited. This is the culmination of a lot of hard work by a lot of people. We’re really proud of the business we’ve built. I mean, building a great company or doing anything important takes time.

TC: Was there something that changed that convinced you to go public after more than a decade of going private, and how do you feel about the pop?

DH: We felt that we were ready. Our business was in great shape. We had a good balance of scale and profitability and growth. As a private company, there are a lot of reasons why it’s been easier to stay private for longer. We’re all proud of the business we’ve built. We see the numbers. We think we’re on to not just a great business, but pioneering a whole new model. We’re taking the best of our consumer roots, combining them with the best parts of software as a service, and it was really gratifying to see investors be excited about it and for the rest of the world to catch on.

TC: As you were on your road show, what were some of the big questions investors were asking?

DH: We don’t fit neatly into any one mold. We’re not a consumer company, and we’re not a traditional enterprise company. We’re basically taking that consumer internet playbook and applying it to business software, combining the virality and scale. Over the last couple years, as we’ve been building that engine, investors are starting to understand that we don’t fit into a traditional mold. The numbers speak to themselves, they can appreciate the unusual combination.

TC: What did you tell them to convince them?

DH: We’re just able to get adoption. Just the fact that we have hundreds of millions of users and we’ve found Dropbox is adopted in millions of companies [was enough evidence]. More than 300,000 of those users are Dropbox Business companies. We spend about half on sales of marketing as a percentage of revenue of a typical software as a service company. Efficiency and scale are the distinctive elements, and investors zero in on that. To be able to acquire customers at that scale and also really efficiently, that’s what makes us stand out. They’ve seen Atlassian be successful with self-serve products, but you can layer on top of that leveraging our freemium and viral elements and our focus on design and building great products.

TC: How do you think about deploying the capital you’ve picked up from the IPO?

DH: So, we’re public because they wanted us to be a public company. But our approach is still the same. First, it’s about getting the best talent in the building and making sure we build the best products, and if you do those things, make sure customers are happy, that’s what works.

TC: What about recruiting?

DH: It’s a big day for dropbox. We’re all really excited about it and hopefully a lot of other people are too.

TC: When you look at your customer acquisition ramp, what does that look like?

DH: I mean, we’ve been making a lot of progress in the past couple of years if you look at growth in subscribers. That will continue. We look at numbers, we have 11 million subscribers, 80% use dropbox for work. But at the same time, we look at the world, there’s 1 billion knowledge workers and growing. We’re not gonna run out of people who need Dropbox.

TC: What about convincing investors about the consumer part of the business? How did you do that?

DH: I think, when you explain that our consumer and cloud storage roots have really become a way for us to efficiently acquire business customers at scale, that helps them understand. Second, it’s easy to focus on how in the consumer realm that the business has been commoditized. There’s all this free space and all this competition. On the other hand, we’ve never lowered prices, we’ve never even given more free space, we know that what our customers really value is the sharing and collaboration, not just the storage. It’s been good to move investors beyond the 2010 understanding of our business.

TC: How did creating your own infrastructure play into your readiness to go public?

DH: When I say that today is the culmination of a lot of events, that’s a great example. We made a many-year investment to migrate off the public cloud. Certainly that was one of the more eye-popping investors watching our gross margins literally double over the last couple of years from burning cash to being cash flow positive. We’ll continue reaching larger and larger scale, and those investments will.

TC: Getting a new guitar any time soon?

DH: I probably should.

Dropbox, after more than a decade, finally went public this morning — and the stock soared more than 40% in its initial trading, making it a marquee success for one of the original Web 2.0 companies (at least for now).

While we still have to wait for the dust to settle, it’s been a very long road for Dropbox. From starting off as a file-sharing service, to hitting a $10 billion valuation in the middle of a massive hype cycle, to expectations dropping and then the announcement of a $1 billion revenue run rate. Dropbox has been a rollercoaster, but it’s another big moment this afternoon: it’s Y Combinator’s first big IPO. And Y Combinator still has a very deep bench of startups that are, thus far, obvious IPO candidates down the line like Airbnb and Stripe.

That isn’t to take away anything from the work of CEO Drew Houston and the rest of Dropbox’s team, but Y Combinator’s job is to basically take a bunch of shots in the dark based on good ideas and potentially savvy founders. Houston was one of the first of a firm that now takes in a hundred-odd founders per class. Y Combinator Founder and partner Jessica Livingston was there for the start of it, recalling back to the day that Houston rushed to her and Paul Graham to show him his little side project.

We caught up with Livingston this morning ahead of the IPO for a short interview. Here’s the conversation, which was lightly edited for clarity:

TC: Can you tell us a little bit about what it’s like to finally see the first Y Combinator company to go public?

JL: I feel like 13 years ago, it was just this dream of ours. It was this seemingly unattainable dream that goes, ‘maybe one of the startups we fund could go public someday.’ That was the holy grail. It’s an exciting day for Y Combinator. It shows what a long game investing is in early-stage startups. I do feel kind of validated.

TC: How did Y Combinator first end up in touch with Houston?

JL: He applied as a solo founder. We had met Drew the summer before. Back then, we were so small that we always encouraged people to bring friends to a Y Combinator dinner. [Xobni founder Adam Smith] brought [Houston], and we met him then and talked it through. When he applied, we invited him to come to an interview, and Paul [Graham] before the interview reached out to [Houston]. He said, “I see you’re a solo founder, and you should find a cofounder.” Three weeks later Drew showed up with [co-founder Arash Ferdowsi]. It was a great match that worked well.

TC: As Dropbox has grown, what’s stood out to you the most during changes in the market?

JL: They’re a classic example of founders who are programmers who built something to solve their own problem. Clearly, this is a perfect example of that. Drew gets on the bus, he forgets his files, and he can’t work on the whole trip down. He then creates something that will allow him to access files from everywhere. At the time, when he came on the scene with that, there were a lot of companies doing it but none were very good. I feel like Dropbox, regardless of market dynamics, from the very beginning was always dedicated to wanting to do well by building a better solution. They wanted to build one that actually works. I feel like they’ve stuck to that and that’s been driving them since. That’s been their guidepost.

TC: What was your first meeting with Houston like, and do you think he has changed in the past 10 years?

JL: When I first met him, he was young — he was very young — and he was always a good hacker, and very earnest. During Y Combinator he was very focused on building this product and was not distracted by other things. That’s when there were just two people. He’s really evolved over the years as an incredible leader. He’s grown this company and he’s navigated through all different parts of his life cycle. I’ve witnessed his growth as a leader and as a human being. He’s always been a great person. It’s sort of exciting to see where he is now that he’s come a long way, it’s really cool.

TC: Houston and Ferdowsi still own significant portions of the company even after raising a lot of venture capital. Do you think Y Combinator had any effect on companies looking for more founder friendly deals?

JL: I think when Y Combinator started, our goal in many ways was to empower founders. It was to level the playing field. You don’t have to have a connection in Silicon Valley to get funding. You just have to apply on our website. You don’t have to have gone to an Ivy League school. We [try to tell them], don’t let investors take advantage of you because you’re young and have never done this before. In general, times have changed over the past 15 years. Hopefully Y Combinator played a small role in some of those changes in making things a little more found friendly.

TC: What’s one of your favorite stories about Houston?

JL: He was always very calm, cool, and collected under pressure. I remember that was definitely a quality about him. His feathers didn’t get ruffled easily. One of the things I remember most clearly is from that summer when we had demo day. Back then it was, like, 40 people tops. Still, there was a lot of pressure. I remember Paul [Graham] came up with this idea that, ‘hey, Drew, during your demo day you should show people how well Dropbox actually works by deleting your presentation live and restoring it through Dropbox.’ That’s kind of risky, right? To delete your presentation. You’re just standing up there without anything. And he did it and he nailed the presentation. It sounds a little gimmicky, but it really worked and showed his product worked. I remember thinking, like, wow, he’s pretty calm. If it were me I don’t think I could hit the delete button in front of these people. That’s an important quality in someone, not to get flustered.

By the way, we funded them in 2007. If you asked me in 2008 how were they doing, I would say, well, they’re making progress. But it wasn’t like we funded them and we could say, ‘this is gonna be a great one.’ We just knew, yeah they’re making progress, but it’s always hard to know there.

TC: Back then, what were you just expecting? M&A? Did you even anticipate an IPO?

JL:  As we were formulating the idea, the hope was rather than going to work at Microsoft — I use them as an example because that was the company back then — and rather than going to get a job out of college, why not build a company and make Microsoft acquire you to get you to work for them? We had low expectations back then. We were hoping there’d be some small acquisitions. But yes, the hope was always acquisitions, but maybe someday in our wildest dreams there’d be an IPO. We didn’t even think YC would work when we started, people didn’t believe in YC’s models for many years.

TC: Looking back, what would you say is one of the biggest things you’ve learned throughout this experience?

JL: What a long road it is for startups. When we started YC back then, it wasn’t a popular thing to do a startup. Now, thank goodness, more people are starting them, and more types of people are starting them. It’s not just super high-tech companies. That’s exciting, but what I think a lot of people don’t realize is how hard startups are. You say, yeah, I know how hard, but people don’t realize how difficult they are and how long the commitment is. If you’re successful, it takes such a long time. For [someone like Houston] to make it to that point, they’ve committed a lot of their life and energy and all their intellectual capacity to making this work. To me, that’s so exciting, but I think it would surprise people to know realistically how long that could take.

TC: What would you tell startups with the hindsight of what happened with Dropbox’s valuation hype cycle?

JL: I will say, with startups, sometimes you just have to stick to what you’re doing. There’s a lot of stuff going on around you, especially now with social media and things like that. With a startup, you just have to keep moving forward with building a company and building a great product.

 Healthy financial milestones sugarcoat the conversation temporarily, but eventually Drew Houston is going to have to step into the public markets. At that point nobody will care how fast Dropbox grew its revenue back in the day. The question will be whether Dropbox is a company that can eventually sustain $10 billion in yearly revenue. Read More

 Dropbox said today that it is rolling out Paper — its note-taking app that it’s emphasizing is a tool that’s built for managing workflow as well — globally.
In addition to the regular launch of Paper, the company said that users will also be able to automatically generate presentations and run them through Paper in their browsers. Radhakrishnan said that users were… Read More